Bromocyclopentane → 2,4,6-Triiodophenoxycyclopentane

HRID 53490Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[C:10]([I:15])[C:9]=1[OH:16].[CH:17]1(Br)[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O>[I:7][C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[C:10]([I:15])[C:9]=1[O:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

Milled, anhydrous potassium carbonate (14.2 g, 103 mmol, 1.2 eq) was added in portions to a stirred solution of 2,4,6-triiodophenol (40.5 g, 85.8 mmol) in 50 ml of dry (4A sieves) dimethylformamide at room temperature. After stirring for 20 minutes, cyclopentyl bromide (12 ml, 112 mmol, 1.3 eq) in dimethylformamide (20 ml) was added and the viscous mixture was gradually heated to 130° C. under argon for approximately 45 minutes. After cooling, the mixture was filtered and the collected solid was washed with chloroform. The filtrate was concentrated in vacuo to give 50 g of an amber oil The crude oily product was partitioned between ethyl acetate (300 ml) and water (500 ml); the organic layer was dried over magnesium sulfate and passed through a short pad of silica gel. The filtrate was treated with decolorizing carbon, filtered, and stripped to give an amber oil. The oil was dried at 60° C. under high vacuum to give 40.4 g (87%) of product.

Workup

customMilled
dry with materialof dry (4A sieves) dimethylformamide at room temperature
temperatureAfter cooling
filtrationthe mixture was filtered
washthe collected solid was washed with chloroform
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4a457aa6459c470db51614492bea822a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620677

Reaction notes

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